DE69702227T2 - Polymer compositions - Google Patents
Polymer compositionsInfo
- Publication number
- DE69702227T2 DE69702227T2 DE69702227T DE69702227T DE69702227T2 DE 69702227 T2 DE69702227 T2 DE 69702227T2 DE 69702227 T DE69702227 T DE 69702227T DE 69702227 T DE69702227 T DE 69702227T DE 69702227 T2 DE69702227 T2 DE 69702227T2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- polymer composition
- aliphatic
- composition according
- phosphono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 229920000642 polymer Polymers 0.000 title claims abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- -1 phosphono - substituted carboxylic acid Chemical class 0.000 claims abstract description 5
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 3
- 229920000768 polyamine Polymers 0.000 claims abstract description 3
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 3
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- KMDMOMDSEVTJTI-UHFFFAOYSA-N 2-phosphonobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)P(O)(O)=O KMDMOMDSEVTJTI-UHFFFAOYSA-N 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004135 Bone phosphate Substances 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- REIOYEWGAMBNBT-UHFFFAOYSA-N (1,4-dimethoxy-1,4-dioxobutan-2-yl)phosphonic acid Chemical compound COC(=O)CC(P(O)(O)=O)C(=O)OC REIOYEWGAMBNBT-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1488—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
- C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Resins (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft Polymer-Zusammensetzungen; insbesondere betrifft diese Erfindung Polymer-Zusammensetzungen, die Phosphono-Substituenten enthalten.The present invention relates to polymer compositions; in particular, this invention relates to polymer compositions containing phosphono substituents.
Mit der vorliegenden Erfindung wird eine Polymer-Zusammensetzung bereitgestellt, bei der es sich um ein Polykondensationsprodukt handelt, das besteht aus:The present invention provides a polymer composition which is a polycondensation product, which consists of:
a) einer Phosphono-substituierten Carbonsäure, oder einem Phosphono-substituierten Carbonsäureester; unda) a phosphono-substituted carboxylic acid, or a phosphono-substituted carboxylic acid ester; and
b) einer Baueinheit, ausgewählt aus:b) a structural unit selected from:
(I) mehrbasischen Alkoholen;(I) polybasic alcohols;
(II) aliphatischen Polycarbonsäuren und aromatischen, einkernigen oder mehrkernigen Polycarbonsäuren;(II) aliphatic polycarboxylic acids and aromatic, mononuclear or polynuclear polycarboxylic acids;
(III) Ester oder Anhydriden der Polycarbonsäuren nach (II);(III) esters or anhydrides of the polycarboxylic acids according to (II);
(IV) aliphatischen und aromatischen Polyaminen, Polyisocyanaten und Polyepoxyden.(IV) aliphatic and aromatic polyamines, polyisocyanates and polyepoxides.
Zweckmäßigerweise kann die Komponente (a) eine aliphatische oder aromatische, Phosphono-substituierte Dicarbonsäure oder ein Ester einer solchen Carbonsäure sein, zum Beispiel Phosphono-bernsteinsäure oder deren Dimethylester.Conveniently, component (a) may be an aliphatic or aromatic phosphono-substituted dicarboxylic acid or an ester of such a carboxylic acid, for example phosphono-succinic acid or its dimethyl ester.
Zweckmäßigerweise kann die Baueinheit (b) ein aliphatischer oder cycloaliphatischer, zweibasischer Alkohol sein, wie etwa Ethylenglykol, Propylenglykol, Neopentylglykol oder 1,4-Dimethylol-cyclohexan.Conveniently, the building block (b) may be an aliphatic or cycloaliphatic dibasic alcohol, such as ethylene glycol, propylene glycol, neopentyl glycol or 1,4-dimethylol-cyclohexane.
Alternativ kann die Baueinheit (b) ein dreibasischer Alkohol sein, wie etwa Glycerol.Alternatively, the building block (b) can be a tribasic alcohol, such as glycerol.
Nach einer weiteren Alternative kann die Baueinheit (b) Bernsteinsäure, Terephthalsäure, Phthalsäureanhydrid, Naphthalsäure oder Naphthalsäureanhydrid sein.According to a further alternative, the building block (b) can be succinic acid, terephthalic acid, phthalic anhydride, naphthalic acid or naphthalic anhydride.
Weiterhin kann die Baueinheit (b) Ethylendiamin sein.Furthermore, the building block (b) can be ethylenediamine.
Nachstehend wird die vorliegende Erfindung mit Bezugnahme auf die folgenden Beispiele weiter erläutert.Hereinafter, the present invention will be further explained with reference to the following examples.
Die nachstehenden Polyester-Zusammensetzungen werden unter Verwendung von Phosphono-bernsteinsäure und verschiedenen mehrbasischen Alkoholen erzeugt:The following polyester compositions are produced using phosphonosuccinic acid and various polybasic alcohols:
Beispiel 1: Mit Neopentylglykol (NPG).Example 1: With neopentyl glycol (NPG).
Beispiel 2: Mit 1,4-dimethylol-cyclohexan (CHDM).Example 2: With 1,4-dimethylol-cyclohexane (CHDM).
Beispiel 3: Mit Ethylenglykol (EG).Example 3: With ethylene glycol (EG).
Equimolare Mengen der Phosphono-bernsteinsäure und jeder der vorstehenden Dialkohole werden in einen 100 ml Rundkolben gegeben. Unter regelmäßiger Kontrolle der Säurezahl läßt man das Reaktionsgemisch bei ungefähr 160ºC mehrere Stunden lang reagieren, bis sich eine sehr viskose Flüssigkeit gebildet hat.Equimolar amounts of phosphonosuccinic acid and each of the above dialcohols are placed in a 100 ml round-bottomed flask. The reaction mixture is allowed to react at about 160°C for several hours, while regularly checking the acid number, until a very viscous liquid has formed.
Die an den erhaltenen Produkten mit Hilfe der Gel-Chromatographie ermittelten, scheinbaren Molekulargewichte sind in der nachstehenden Tabelle aufgeführt. Bei diesen Werten handelt es sich lediglich um angenäherte Werte, weil die Polymere sehr polar sind. Die tatsächlichen Molekulargewichte werden höher erwartet, als die angegebenen scheinbaren Molekulargewichte. The apparent molecular weights determined on the products obtained by gel chromatography are shown in the table below. These values are only approximate because the polymers are very polar. The actual molecular weights are expected to be higher than the apparent molecular weights given.
* mittleres gewichtsmässiges Molekulargewicht* weight average molecular weight
Polyester mit Phosphono-bernsteinsäure-endgruppen werden nach folgendem Verfahren erhalten:Polyesters with phosphonosuccinic acid end groups are obtained by the following process:
Neopentylglykol (81, 797g; 0, 786 Mol) und Bernsteinsäureanhydrid (77,000 g; 0, 769 Mol) werden in einen 250 ml Kunststofftopf gegeben, der mit einem mechanischen Rührwerk, einem Temperaturfühler, einem Stickstoffeinlaß und einem Destillieransatz ausgerüstet ist. Mit Hilfe eines Isoliermantels wird das Reaktionsgemisch unter Rühren auf 160ºC erwärmt. Nachdem das Gemisch geschmolzen ist, wird Stickstoff durch das Reaktionsgemisch geperlt. Im Verlauf von 40 Stunden wird das Reaktionsgemisch von 160ºC auf 190ºC erwärmt. Anschließend wird eine Probe des erhaltenen Zwischenproduktes genommen.Neopentyl glycol (81.797 g; 0.786 mol) and succinic anhydride (77.000 g; 0.769 mol) are placed in a 250 ml plastic pot equipped with a mechanical stirrer, a temperature sensor, a nitrogen inlet and a distillation head. Using an insulating jacket, the reaction mixture is heated to 160ºC while stirring. After the mixture has melted, nitrogen is bubbled through the reaction mixture. Over the course of 40 hours, the reaction mixture is heated from 160ºC to 190ºC. A sample of the resulting intermediate is then taken.
Daraufhin wird die Temperatur auf 100ºC abgesenkt und Phosphonobernsteinsäure (3,078 g; 0,016 Mol) hinzugefügt. Das Reaktionsgemisch wird erneut 5,5 Stunden lang auf 160ºC erwärmt. Daraufhin läßt man auf Raumtemperatur abkühlen. Das erhaltene Produkt wird aus Ethylacetat umkristallisiert und bildet ein feines, weißes Pulver.The temperature is then lowered to 100ºC and phosphonosuccinic acid (3.078 g; 0.016 mol) is added. The reaction mixture is again heated to 160ºC for 5.5 hours. It is then allowed to cool to room temperature. The product obtained is recrystallized from ethyl acetate and forms a fine white powder.
Mit Hilfe der Gel-Chromatographie wird das Molekulargewicht des Zwischenproduktes zu etwa 20.000 g/Mol bestimmt.Gel chromatography is used to determine the molecular weight of the intermediate product was determined to be about 20,000 g/mol.
Im wesentlichen wird das vorstehend unter Ziffer 2.1.1 beschriebene Verfahren wiederholt; abweichend wird Bensteinsäureanhydrid durch Phthalsäureanhydrid ersetzt.Essentially, the procedure described above under section 2.1.1 is repeated; the only difference is that succinic anhydride is replaced by phthalic anhydride.
Es wird ein festes Polymer mit emulgierenden Eigenschaften erhalten.A solid polymer with emulsifying properties is obtained.
Claims (7)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9610070A GB2313126A (en) | 1996-05-14 | 1996-05-14 | Polymer compositions containing phosphorus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69702227D1 DE69702227D1 (en) | 2000-07-13 |
| DE69702227T2 true DE69702227T2 (en) | 2000-12-21 |
Family
ID=10793685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69702227T Expired - Lifetime DE69702227T2 (en) | 1996-05-14 | 1997-04-25 | Polymer compositions |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6111061A (en) |
| EP (1) | EP0807654B1 (en) |
| JP (1) | JPH1081755A (en) |
| KR (1) | KR970074823A (en) |
| AT (1) | ATE193714T1 (en) |
| CA (1) | CA2204072A1 (en) |
| DE (1) | DE69702227T2 (en) |
| DK (1) | DK0807654T3 (en) |
| ES (1) | ES2148905T3 (en) |
| GB (1) | GB2313126A (en) |
| GR (1) | GR3034102T3 (en) |
| NO (1) | NO312966B1 (en) |
| PT (1) | PT807654E (en) |
| TW (1) | TW412566B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2231746T3 (en) * | 2008-01-11 | 2017-03-31 | The Sherwin-Williams Company | Metal coating composition |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764570A (en) * | 1969-05-05 | 1973-10-09 | Armstrong Cork Co | Polyurethane foams from phosphorous containing sugar polyols |
| BE814388A (en) * | 1973-05-05 | 1974-10-30 | PHOSPHONOCARBOXYLIC ACID ESTERS | |
| US4157436A (en) * | 1975-10-14 | 1979-06-05 | Toyo Boseki Kabushiki Kaisha | Phosphorus-containing polyesters |
| DE2708790C2 (en) * | 1977-03-01 | 1982-02-25 | Akzo Gmbh, 5600 Wuppertal | Linear homo- or copolyesters, process for making the polyesters and their uses |
| DE4119054A1 (en) * | 1990-06-18 | 1991-12-19 | Sandoz Ag | POLYAETHERESTERS, THEIR PRODUCTION AND USE |
| IT1251154B (en) * | 1991-08-07 | 1995-05-04 | Enichem Sintesi | PENTAERITRIL PHOSPHONATES AND THEIR USE IN SELF-EXTINGUISHING THERMOPLASTIC POLYMER COMPOSITIONS |
| DE4141928A1 (en) * | 1991-12-19 | 1993-06-24 | Boehringer Mannheim Gmbh | NEW PHOSPHON AMBER ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| US5496476A (en) * | 1992-12-21 | 1996-03-05 | Ppg Indutstries, Inc. | Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic acid |
| DE4408478A1 (en) * | 1994-03-14 | 1995-09-21 | Bayer Ag | Water treatment agents |
| IT1269850B (en) * | 1994-05-27 | 1997-04-15 | Enichem Sintesi | NEW POLI (PENTAERITRIL DIPHOSPHONATE) AND ITS USE IN SELF-EXTINGUISHING THERMOPLASTIC POLYMERIC COMPOSITIONS |
| US5478919A (en) * | 1994-07-29 | 1995-12-26 | Donlar Corporation | Aspartic acid copolymers and their preparation |
-
1996
- 1996-05-14 GB GB9610070A patent/GB2313126A/en not_active Withdrawn
-
1997
- 1997-04-25 EP EP97302878A patent/EP0807654B1/en not_active Expired - Lifetime
- 1997-04-25 DK DK97302878T patent/DK0807654T3/en active
- 1997-04-25 DE DE69702227T patent/DE69702227T2/en not_active Expired - Lifetime
- 1997-04-25 ES ES97302878T patent/ES2148905T3/en not_active Expired - Lifetime
- 1997-04-25 PT PT97302878T patent/PT807654E/en unknown
- 1997-04-25 AT AT97302878T patent/ATE193714T1/en not_active IP Right Cessation
- 1997-04-29 KR KR1019970016335A patent/KR970074823A/en not_active Application Discontinuation
- 1997-04-30 CA CA002204072A patent/CA2204072A1/en not_active Abandoned
- 1997-05-08 US US08/853,166 patent/US6111061A/en not_active Expired - Fee Related
- 1997-05-13 JP JP9122539A patent/JPH1081755A/en active Pending
- 1997-05-13 NO NO19972183A patent/NO312966B1/en unknown
- 1997-05-26 TW TW086107081A patent/TW412566B/en not_active IP Right Cessation
-
2000
- 2000-08-02 GR GR20000401799T patent/GR3034102T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO972183L (en) | 1997-11-17 |
| EP0807654A2 (en) | 1997-11-19 |
| ES2148905T3 (en) | 2000-10-16 |
| MX9703608A (en) | 1998-06-30 |
| GR3034102T3 (en) | 2000-11-30 |
| EP0807654A3 (en) | 1998-03-25 |
| US6111061A (en) | 2000-08-29 |
| DK0807654T3 (en) | 2000-08-07 |
| GB9610070D0 (en) | 1996-07-17 |
| NO972183D0 (en) | 1997-05-13 |
| GB2313126A (en) | 1997-11-19 |
| PT807654E (en) | 2000-09-29 |
| DE69702227D1 (en) | 2000-07-13 |
| CA2204072A1 (en) | 1997-11-14 |
| EP0807654B1 (en) | 2000-06-07 |
| KR970074823A (en) | 1997-12-10 |
| NO312966B1 (en) | 2002-07-22 |
| ATE193714T1 (en) | 2000-06-15 |
| TW412566B (en) | 2000-11-21 |
| JPH1081755A (en) | 1998-03-31 |
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